How to Tackle a Stretch Assignment

The question was, paraphrased, how do I handle a promotion I’m not ready for? My prior boss left, now I have his role, and I get asked to do things I don’t understand how to do. I feel frustrated. I have one person who will help me by answering my questions, but if I ask more than three, he gets mad.

My reply (originally published on StackExchange):

How to Tackle a Stretch Assignment

My friend, you’re in a wonderful situation. It’s called a STRETCH ASSIGNMENT.

You’re highly uncomfortable, I get it. Set that aside for just a moment and let’s look at this from your director’s perspective. Then I’ll offer you some guidance, including how to get the most help from others without them getting mad.

YOUR BOSS (the director)

Your director believed you were the best available person to fill this need. Otherwise you wouldn’t have gotten it.

If you merely kick it back up to the director, now he has to start all over finding a new person, AND (as Joe correctly says elsewhere on this page), you’ll be seen as someone who doesn’t want to grow or take on new responsibilities. (Regardless of how true that is or not.) Such a reputation will not help your career.

Put yourself in his shoes. What he really hopes you’ll say is something like:

“Boss, I’m out of my depth here, and if you believe I can do this, then I’m totally willing to learn what I need to learn, so I can do a good job. I’m going to need your support to do this. Is it okay for me to learn on the job, or would it be better for the company to find someone who already knows what I don’t know?”

Assume he says YES. Next question you ask is:

“To keep myself prioritized, which results are the most important results you want me to deliver? Here’s a list of what I think you want from my position, and I’ve done my best to order it in what I think is the right order of importance.”

(At this point the director may faint from happiness.)

Now you just supply a list of education you need — courses, mentoring, etc.

How to Ask for Help Successfully

The short summary of “how to ask for help successfully” is, make it easy on the other person. That means:

  • Spread the questions out — don’t only ask one person
  • Remember answers so you don’t ask twice
  • Keep a log of questions and answers and study that log for patterns
  • Queue up non-urgent questions so you can ask them in batches
  • Do favors for your helpers. Buy lunch. Buy scotch.
  • Ask smart questions that show you researched the issue, and come in to the session with what you THINK is the right answer for each question — this speeds your learning and shows your helper that you’re not just a lazy dumb guy who wants others to do his job for him

The skills you’ll learn handling this situation — how to see things from your boss’s perspective, and how to ask for help successfully — will pay off for the rest of your career.

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